Novel boron compound and organic light-emitting diode comprising same

ABSTRACT

The present disclosure relates to a boron compound useful in an organic light-emitting diode and an organic light-emitting diode comprising same and, more particularly, to a boron compound represented by any one of [Chemical Formula A] to [Chemical Formula C], wherein [Chemical Formula A] to [Chemical Formula C] are as defined in the description.

TECHNICAL FIELD

The present disclosure relates to a novel boron compound useful for anorganic light-emitting diode and, more particularly, to a novel boroncompound that can be used as a dopant material in an organiclight-emitting diode and allow for excellent diode characteristicsincluding high luminous efficiency and low driving voltage, and anorganic light-emitting diode comprising the boron compound.

BACKGROUND ART

Organic light-emitting diodes (OLEDs), based on self-luminescence, areused to create digital displays with the advantage of having a wideviewing angle and being able to be made thinner and lighter than liquidcrystal displays. In addition, an OLED display exhibits a very fastresponse time. Accordingly, OLEDs find applications in the full colordisplay field or the illumination field.

In general, the term “organic light-emitting phenomenon” refers to aphenomenon in which electrical energy is converted to light energy bymeans of an organic material. An organic light-emitting diode using theorganic light-emitting phenomenon has a structure usually including ananode, a cathode, and an organic material layer interposed therebetween.In this regard, the organic material layer may have, for the most part,a multilayer structure consisting of different materials, for example, ahole injection layer, a hole transport layer, a light-emitting layer, anelectron transport layer, and an electron injection layer in order toenhance the efficiency and stability of the organic light-emittingdiode. In the organic light-emitting diode having such a structure,application of a voltage between the two electrodes injects a hole fromthe anode and an electron from the cathode to the organic layer. In theluminescent zone, the hole and the electron recombine to produce anexciton. When the exciton returns to the ground state from the excitedstate, the molecule of the organic layer emits light. Such an organiclight-emitting diode is known to have characteristics such asself-luminescence, high luminance, high efficiency, low driving voltage,a wide viewing angle, high contrast, and high-speed response.

Materials used as organic layers in OLEDs may be divided according tofunctions into luminescent materials and charge transport materials, forexample, a hole injection material, a hole transport material, anelectron transport material, and an electron injection material and, asneeded, further into an electron-blocking material or a hole-blockingmaterial.

As for the luminescent materials, there are two main families of OLED:those based on small molecules and those employing polymers. Thelight-emitting mechanism forms the basis of classification ofluminescent materials as fluorescent and phosphorescent materials, whichuse excitons in singlet and triplet states, respectively.

When a single material is employed as the luminescent material,intermolecular actions cause the maximum luminescence wavelength toshift toward a longer wavelength, resulting in a reduction in colorpurity and luminous efficiency due to light attenuation. In this regard,a host-dopant system may be used as a luminescent material so as toincrease the color purity and the luminous efficiency through energytransfer.

This is based on the principle whereby, when a dopant which is smallerin energy band gap than a host forming a light-emitting layer is addedin a small amount to the light-emitting layer, excitons are generatedfrom the light-emitting layer and transported to the dopant, emittinglight at high efficiency. Here, light with desired wavelengths can beobtained depending on the kind of the dopant because the wavelength ofthe host moves to the wavelength range of the dopant.

Meanwhile, studies have been made to use boron compounds as dopantcompounds. With regard to related art pertaining to the use of boroncompounds, reference may be made to Korean Patent No. 10-2016-0119683 A(issued Oct. 14, 2016), which discloses an organic light-emitting diodeemploying a novel polycyclic aromatic compound in which multiplearomatic rings are connected via boron and oxygen atoms. In addition,International Patent No. WO 2017/188111 (Nov. 2, 2017) disclosed anorganic light emitting diode in which a compound structured to connectmultiple polycondensed aromatic rings via boron and nitrogen atoms isused as a dopant in a light emitting layer while an anthracenederivative is used as a host.

Despite a variety of kinds of compounds prepared for use in lightemitting layers in organic light emitting diodes including the relatedarts, there is still a continuing need to develop a novel compound thatallows an OLED to be stably driven at a lower voltage and exhibits highefficiency, and an OLED including the same.

DISCLOSURE Technical Problem

Therefore, an aspect of the present disclosure is to provide a boroncompound having a novel structure which can be used as a dopant materialin a light-emitting layer of an organic light-emitting diode.

In addition, another aspect of the present invention is to provide anorganic light-emitting diode (OLED) having the boron compound applied asa dopant material therein and exhibiting excellent diode characteristicsincluding high luminous efficiency and low-voltage driving.

Technical Solution

In order to accomplish the purposes, the present disclosure provides aboron compound represented by any one of the following Chemical FormulasA to C:

wherein,

Q₁ to Q₃, which may be the same or different, are each independently asubstituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbonatoms, or a substituted or unsubstituted heteroaromatic ring of 2 to 50carbon atoms,

Y is any one selected from N—R₃, CR₄R₅, O, S, and Se,

X is any one selected from B, P and P═O and

R₃ to R₅, which may be the same or different, are each independently anyone selected from a hydrogen atom, a deuterium, a substituted orunsubstituted alkyl of 1 to 30 carbon atoms, a substituted orunsubstituted aryl of 6 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted arylamine of 5 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted orunsubstituted arylsilyl of 5 to 30 carbon atoms, a nitro, a cyano, and ahalogen,

R₃ to R₅ may each be connected to the Q₂ ring moiety or Q₃ ring moietyto form an additional mono- or polycyclic aliphatic or aromatic ring and

R₄ and R₅ may be connected to each other to form an additional mono- orpolycyclic aliphatic or aromatic ring,

Cy1 is a substituted or unsubstituted alkylene of 1 to 10 carbon atomsto form a ring with the nitrogen (N) atom, the aromatic carbon atom ofQ₁ to which the nitrogen (N) atom is connected, and the aromatic carbonatom of Q₁ to which Cy1 is to bond,

Cy2 in Chemical formula B is a substituted or unsubstituted alkylene of1 to 10 carbon atoms to form a saturated hydrocarbon ring added to Cy1,together with the carbon atoms of Cy1,

and Cy3 in Chemical Formula C is a substituted or unsubstituted alkyleneof 1 to 10 carbon atoms to form a ring with the aromatic carbon atom ofQ₃ to which Cy3 is to bond, the aromatic carbon atom of Q₃ to which thenitrogen (N) atom is connected, the nitrogen (N) atom, and the carbonatom of Cy1 to which the nitrogen (N) atom is connected.

Advantageous Effects

When used as a dopant material, the novel compound according to thepresent disclosure allows for the provision of an organic light-emittingdiode that can be driven at a lower voltage with improved luminousefficiency, compared to conventional organic light-emitting diodes.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic diagram of an organic light-emitting diodeaccording to some embodiments of the present disclosure.

MODE FOR CARRYING OUT THE INVENTION

Below, a detailed description will be given of the present disclosure.In each drawing of the present disclosure, sizes or scales of componentsmay be enlarged or reduced from their actual sizes or scales for betterillustration, and known components may not be depicted therein toclearly show features of the present disclosure. Therefore, the presentdisclosure is not limited to the drawings. When describing the principleof the embodiments of the present disclosure in detail, details ofwell-known functions and features may be omitted to avoid unnecessarilyobscuring the presented embodiments.

In drawings, for convenience of description, sizes of components may beexaggerated for clarity. For example, since sizes and thicknesses ofcomponents in drawings are arbitrarily shown for convenience ofdescription, the sizes and thicknesses are not limited thereto.Furthermore, throughout the description, the terms “on” and “over” areused to refer to the relative positioning, and mean not only that onecomponent or layer is directly disposed on another component or layerbut also that one component or layer is indirectly disposed on anothercomponent or layer with a further component or layer being interposedtherebetween. Also, spatially relative terms, such as “below”,“beneath”, “lower”, and “between” may be used herein for ease ofdescription to refer to the relative positioning.

Throughout the specification, when a portion may “include” a certainconstituent element, unless explicitly described to the contrary, it maynot be construed to exclude another constituent element but may beconstrued to further include other constituent elements. Further,throughout the specification, the word “on” means positioning on orbelow the object portion, but does not essentially mean positioning onthe lower side of the object portion based on a gravity direction.

The present disclosure provides a boron compound represented by any oneof the following Chemical Formulas A to C:

wherein,

Q₁ to Q₃, which may be the same or different, are each independently asubstituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbonatoms, or a substituted or unsubstituted heteroaromatic ring of 2 to 50carbon atoms,

Y is any one selected from N—R₃, CR₄R₅, O, S, and Se,

X is any one selected from B, P and P═O and

R₃ to R₅, which may be the same or different, are each independently anyone selected from a hydrogen atom, a deuterium, a substituted orunsubstituted alkyl of 1 to 30 carbon atoms, a substituted orunsubstituted aryl of 6 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted arylamine of 5 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted orunsubstituted arylsilyl of 5 to 30 carbon atoms, a nitro, a cyano, and ahalogen,

R₃ to R₅ may each be connected to the Q₂ ring moiety or Q₃ ring moietyto form an additional mono- or polycyclic aliphatic or aromatic ring and

R₄ and R₅ may be connected to each other to form an additional mono- orpolycyclic aliphatic or aromatic ring,

Cy1 is a substituted or unsubstituted alkylene of 1 to 10 carbon atomsto form a ring with the nitrogen (N) atom, the aromatic carbon atom ofQ₁ to which the nitrogen (N) atom is connected, and the aromatic carbonatom of Q₁ to which Cy1 is to bond,

Cy2 in Chemical formula B is a substituted or unsubstituted alkylene of1 to 10 carbon atoms to form a saturated hydrocarbon ring added to Cy1,together with the carbon atoms of Cy1,

and Cy3 in Chemical Formula C is a substituted or unsubstituted alkyleneof 1 to 10 carbon atoms to form a ring with the aromatic carbon atom ofQ₃ to which Cy3 is to bond, the aromatic carbon atom of Q₃ to which thenitrogen (N) atom is connected, the nitrogen (N) atom, and the carbonatom of Cy1 to which the nitrogen (N) atom is connected,

wherein, the term ‘substituted in the expression “substituted orunsubstituted” used for compounds of Chemical Formulas A to C meanshaving at least one substituent selected from the group consisting of adeuterium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, an alkenylof 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, aheteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, anarylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms,a heteroaryl of 2 to 50 carbon atoms, a heteroarylalkyl of 2 to 24carbon atoms, an alkoxy of 1 to 24 carbon atoms, an alkylamino of 1 to24 carbon atoms, an arylamino of 6 to 24 carbon atoms, a heteroarylaminoof 1 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, anarylsilyl of 6 to 24 carbon atoms, and an aryloxy of 6 to 24 carbonatoms.

The expression indicating the number of carbon atoms, such as “asubstituted or unsubstituted alkyl of 1 to 30 carbon atoms”, “asubstituted or unsubstituted aryl of 6 to 50 carbon atoms”, etc. meansthe total number of carbon atoms of, for example, the alkyl or arylradical or moiety alone, exclusive of the number of carbon atoms ofsubstituents attached thereto. For instance, a phenyl group with a butylat the para position falls within the scope of an aryl of 6 carbonatoms, even though it is substituted with a butyl radical of 4 carbonatoms.

As used herein, the term “aryl” means an organic radical derived from anaromatic hydrocarbon by removing one hydrogen that is bonded to thearomatic hydrocarbon. The aromatic system may include a fused ring thatis formed by adjacent substituents on the aryl radical.

Concrete examples of the aryl include phenyl, o-biphenyl, m-biphenyl,p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, naphthyl, anthryl,phenanthryl, pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, perylenyl,chrysenyl, naphthacenyl, and fluoranthenyl. At least one hydrogen atomof the aryl may be substituted by a deuterium atom, a halogen atom, ahydroxy, a nitro, a cyano, a silyl, an amino (—NH₂, —NH(R), —N(R′) (R″)wherein R′ and R″ are each independently an alkyl of 1 to 10 carbonatoms, in this case, called “alkylamino”), an amidino, a hydrazine, ahydrazone, a carboxyl, a sulfonic acid, a phosphoric acid, an alkyl of 1to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, analkenyl of 1 to 24 carbon atoms, an alkynyl of 1 to 24 carbon atoms, aheteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, anarylalkyl of 6 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms,or a heteroarylalkyl of 2 to 24 carbon atoms.

The term “heteroaryl substituent” used in the compound of the presentdisclosure refers to a hetero aromatic radical of 2 to 50 carbon atoms,preferably 2 to 24 carbon atoms, bearing 1 to 3 heteroatoms selectedfrom among N, O, P, Si, S, Ge, Se, and Te. In the aromatic radical, twoor more rings may be fused. One or more hydrogen atoms on the heteroarylmay be substituted by the same substituents as on the aryl.

In addition, the term “heteroaromatic ring”, as used herein, refers toan aromatic hydrocarbon ring bearing at least one heteroatom as aromaticring member. In the heteroaromatic ring, one to three carbon atoms ofthe aromatic hydrocarbon may be substituted by at least one selectedparticularly from N, O, P, Si, S, Ge, Se, and Te.

Examples of the alkyl substituent useful in the present disclosureinclude methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl,tert-butyl, pentyl, isoamyl, and hexyl. At least one hydrogen atom ofthe alkyl may be substituted by the same substituent as in the aryl.

Concrete examples of the alkoxy include methoxy, ethoxy, propoxy,isobutoxy, sec-butoxy, pentyloxy, iso-amyloxy, and hexyloxy. One or morehydrogen atoms on the alkoxy may be substituted by the same substituentsas on the aryl.

Concrete examples of the silyl radicals used in the compounds of thepresent disclosure include trimethylsilyl, triethylsilyl,triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl,diphenylmethylsilyl, diphenylvinlysilyl, methylcyclobutylsilyl, anddimethyl furylsilyl. One or more hydrogen atoms on the silyl may besubstituted by the same substituents as on the aryl.

In the present disclosure, the boron compound represented by any one ofChemical Formulas A to C is characterized by the structure in which theQ₁ to Q₃ ring moieties, which are each independently a substituted orunsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms or asubstituted or unsubstituted heteroaromatic ring of 2 to 50 carbonatoms, are connected to one another via the central atom (X), with alinkage between the Q₁ and the Q₃ ring moiety through a nitrogen (N)atom and between the Q₂ and the Q₃ ring moiety through the linker Y,

wherein the nitrogen atom and the Q₁ ring form a fused ring with thesaturated alkylene linker Cy1 (Chemical Formula A), plus the structuraloption that in Chemical Formula B, the saturated alkylene linker Cy2 isadded to form an additional ring fused to the structure of ChemicalFormula A or that in Chemical Formula C, the carbon atom of Cy1 to bebonded to the nitrogen atom and a carbon atom of Q₃ are linked throughthe saturated alkylene linker Cy3 to form a ring fused to the structureof Chemical Formula A

Here, “Cy1” in Chemical Formulas A to C is linked to the nitrogen (N)atom and an aromatic carbon atom of Q₁ to which Cy1 is to bond to form afused ring including the nitrogen atom, the aromatic carbon atom of Q₁to which the nitrogen (N) atom is connected, and the aromatic carbonatom of Q₁ to which Cy1 is to bond, wherein the ring formed by Cy1 is asubstituted or unsubstituted alkylene of 1 to 10 carbon atoms,particularly an alkylene of 2 to 7 atoms, and more particularly analkylene of 2 to carbon atoms, except for the nitrogen (N) atom, thearomatic carbon atom of Q₁ to which the nitrogen (N) atom is connected,and the aromatic carbon atom of Q₁ to which Cy1 is to bond.

The ring formed by “Cy2” in Chemical Formula B may be a substituted orunsubstituted alkylene of 1 to 10 carbon atoms, particularly an alkyleneof 2 to 7 carbon atoms, and more particularly an alkylene of 2 to 5,except for the carbon atoms included in Cy1.

“Cy3” in Chemical Formula C is linked to the carbon atom of Cy1 to whichthe nitrogen (N) atom is connected and the aromatic carbon atom of Q₃ towhich the Cy3 is connected to form a fused ring including the aromaticcarbon atom of Q₃ to which Cy3 is to bond, the nitrogen (N) atom, andthe carbon atom of Cy1 to which the nitrogen (N) atom is connected,wherein the ring formed by Cy3 may be a substituted or unsubstitutedalkylene of 1 to 10 carbon atoms, particularly an alkylene of 2 to 7carbon atoms, and more particularly an alkylene of 3 to 5 carbon atoms,except for the aromatic carbon atom of Q₃ to which Cy3 is to bond, thearomatic carbon atom of Q₃ to which the nitrogen (N) atom is connected,the nitrogen (N) atom, and the carbon atom of Cy1 to which the nitrogen(N) atom is connected.

In an embodiment, the linker Y in Chemical Formulas A to C through whichthe Q₂ and Q₃ ring moieties are linked to each other may be N—R₃ whereinR₃ is as defined above.

In addition, when the linker Y in Chemical Formulas A to C is N—R₃, R₃may be particularly a substituted or unsubstituted aryl of 6 to 50carbon atoms or a substituted or unsubstituted heteroaryl of 2 to 50carbon atoms.

Moreover, Y in Chemical Formulas A to C may be a linker represented bythe following Structural Formula A:

wherein “—*” denotes a bonding site at which the linker Y bonds to anaromatic carbon atom within the Q₂ and Q₃ ring moieties,

R₄₁ to R₄₅, which may be the same or different, are each independentlyany one selected from a hydrogen atom, a deuterium atom, a substitutedor unsubstituted alkyl of 1 to 30 carbon atoms, a substituted orunsubstituted aryl of 6 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted arylamine of 5 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted orunsubstituted arylsilyl of 5 to 30 carbon atoms, a nitro, a cyano, and ahalogen.

In Chemical Formulas A to C, the linker Y may be an oxygen atom.Moreover, in Chemical Formulas A to C, the central atom X may be a boron(B) atom.

In Chemical Formulas A to C, the Q₁ to Q₃ ring moieties, which arebonded to the central atom X, may be the same or different and may eachbe independently a substituted or unsubstituted aromatic hydrocarbonring of 6 to 50 carbon atoms.

In this regard, the aromatic hydrocarbon ring moiety Q₂ in ChemicalFormulas A to C is any one selected from compounds represented by thefollowing Structural Formulas 10 to 21:

wherein, “—*” denotes a bonding site at which a carbon atom in thearomatic ring of Q₂ bonds to X and the linker Y,

R's, which may be the same or different, are each independently ahydrogen, a deuterium, a substituted or unsubstituted alkyl of 1 to 30carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbonatoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbonatoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbonatoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, asubstituted or unsubstituted aryloxy of 6 to 30 carbon atoms, asubstituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, asubstituted or unsubstituted arylthioxy of 5 to 30 carbon atoms, asubstituted or unsubstituted alkylamine of 1 to 30 carbon atoms, asubstituted or unsubstituted arylamine of 5 to 30 carbon atoms, asubstituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, a cyano,and a halogen, and

m is an integer of 1 to 8, wherein when m is two or more or two or moreR's are present, the corresponding R's may be the same or different.

In the case where when the Q₁ to Q₃ are the same or different and areeach independently a substituted or unsubstituted aromatic hydrocarbonring of 6 to 50 carbon atoms, the aromatic hydrocarbon rings of Q₁ andQ₃ in Chemical Formulas A and B may be the same or different and mayeach be independently a ring represented by the following StructuralFormula B,

the aromatic hydrocarbon ring of Q1 in Chemical Formula C may be a ringrepresented by the following Structural Formula B:

wherein “—*” denotes bonding sites at which the corresponding carbons inthe aromatic ring of Q₁ bond to the nitrogen (N) atom and Cy1,respectively or at which the corresponding carbons in the aromatic ringin Q₃ bond to X, the linker Y, and the nitrogen (N) atom, respectively,and

R₅₅ to R₅₇, which may be the same or different, are each independentlyany one selected from a hydrogen, a deuterium, a substituted orunsubstituted alkyl of 1 to 30 carbon atoms, a substituted orunsubstituted aryl of 6 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted arylamine of 5 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted orunsubstituted arylsilyl of 5 to 30 carbon atoms, a cyano, and a halogen,and

any adjacent two of R₅₅ to R₅₇ may be linked to each to each other toform an additional mono- or polycyclic aliphatic or aromatic ring.

In the case where the Q₁ to Q₃ ring moieties are the same or differentand each independently a substituted or unsubstituted aromatichydrocarbon ring of 6 to 50 carbon atoms, the aromatic hydrocarbon ringof Q₃ in Chemical Formula C may be represented by the followingStructural Formula C:

wherein, “—*” denotes bonding sites at which the corresponding carbonsin the aromatic ring of Q₃ bond to the linker Y, X, the nitrogen (N)atom, and Cy3, respectively, and

R₅₈ and R₅₉, which may the same or different, are each independently anyone selected from a hydrogen atom, a deuterium atom, a substituted orunsubstituted alkyl of 1 to 30 carbon atoms, a substituted orunsubstituted aryl of 6 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryoxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted arylamine of 5 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted orunsubstituted arylsilyl of 5 to 30 carbon atoms, a cyano, and a halogen,and

R₅₈ and R₅₉ may be linked to each other to form an additional mono- orpolycyclic aliphatic or aromatic ring.

In addition, Cy1, which forms a ring with the nitrogen (N) atom and acarbon atom of the aromatic ring of Q1 in Chemical Formulas A to C, maybe a linker represented by Structural Formula D:

wherein “—*” denotes a bonding site to a carbon within the aromatic ringof Q₁ or to the nitrogen atom,

B is a single bond or —C(R₆₅) (R₆₆)— or —C(R₆₅) (R₆₆)—C(R₆₇) (R₆₈)—, and

substituents R₆₁ to R₆₈, which may be the same or different, are eachindependently selected from a hydrogen atom, a deuterium atom, ahalogen, a substituted or unsubstituted alkyl of 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl of 3 to 20 carbon atoms, asubstituted or unsubstituted aryl of 6 to 20 carbon atoms, a substitutedor unsubstituted heteroaryl of 2 to 20 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 20 carbon atoms, a substituted orunsubstituted arylsilyl of 6 to 320 carbon atoms, wherein the term‘substituted in the expression “substituted or unsubstituted” used is asdefined above.

In addition, the ring formed by Cy1, Cy2, the nitrogen atom, and Q₁ inChemical Formula B of the present disclosure may be a ring representedby the following Structural Formula E:

wherein, “—*” denotes a bonding site to a carbon atom within thearomatic ring of Q₃,

B is a single bond or —C(R₆₅) (R₆₆)— or —C(R₆₅) (R₆₆)—C(R₆₇) (R₆₈)—,

Substituents R₆₃ to R₆₈, which may be the same or different, are eachindependently selected from a hydrogen atom, a deuterium atom, ahalogen, a substituted or unsubstituted alkyl of 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl of 3 to 20 carbon atoms, asubstituted or unsubstituted aryl of 6 to 20 carbon atoms, a substitutedor unsubstituted heteroaryl of 2 to 20 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 20 carbon atoms, a substituted orunsubstituted arylsilyl of 6 to 320 carbon atoms, and

Cy₄ is a substituted or unsubstituted alkylene of 2 to 5 carbon atoms,with a methylene (—CH₂—) given for each end, wherein the term‘substituted in the expression “substituted or unsubstituted” used is asdefined above.

In an embodiment, at least one of Q1 to Q3 in Chemical Formulas A to Cof the present disclosure may be an aromatic hydrocarbon ring of 6 to 50carbon atoms or an aromatic heteroring of 2 to 50 carbon atoms, eachhaving an arylamino represented the following Structural Formula Fbonded thereto:

wherein, “—*” denotes a bonding site to at least one of Q₁ to Q₃, and

Ar₁₁ and Ar₁₂, which may be the same or different, are each Windependently a substituted or unsubstituted aryl of 6 to 12 carbonatoms.

In an embodiment, the boron compound represented by Chemical Formulas Ato C may be any one selected from the following <Compound 1> to<Compound 132>:

In particular some embodiments thereof, the present disclosure providesan organic light-emitting diode comprising: a first electrode; a secondelectrode facing the second electrode; and an organic layer interposedbetween the first electrode and the second electrode, wherein theorganic layer includes a boron compound represented by any one ofChemical Formulas A to C.

Throughout the description of the present disclosure, the phrase “(anorganic layer) includes at least one organic compound” may be construedto mean that “(an organic layer) may include a single organic compoundspecies or two or more difference species of organic compounds fallingwithin the scope of the present disclosure”.

In this regard, the organic light-emitting diode according to thepresent disclosure may include at least one of a hole injection layer, ahole transport layer, a functional layer capable of both hole injectionand hole transport, a light-emitting layer, an electron transport layer,an electron injection layer, and a capping layer.

In more particular embodiments of the present disclosure, the organiclayer disposed between the first electrode and the second electrodeincludes a light-emitting layer composed of a host and a dopant, whereinthe boron compound represented by any one of Chemical Formulas A to Cserves as the dopant.

In an embodiment, an anthracene derivative represented by the followingChemical Formula D may be used as a host in the organic light-emittingdiode according to the present invention:

wherein,

R₁₁ to R₁₈, which are the same or different, are each as defined for R₃to R₅ in the boron compound above;

Arg and Ar₁₀, which are the same or different, are each independentlyany one selected from a hydrogen atom, a deuterium atom, a substitutedor unsubstituted alkyl of 1 to 30 carbon atoms, a substituted orunsubstituted aryl of 6 to 50 carbon atoms, a substituted orunsubstituted alkenyl of 2 to 30 carbon atoms, a substituted orunsubstituted alkynyl 2 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted cycloalkenyl 5 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted aryamine of 6 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, and a substituted orunsubstituted arylsilyl of 6 to 30 carbon atoms;

L₁₃, which functions as a linker, is a single bond or is selected from asubstituted or unsubstituted arylene of 6 to 20 carbon atoms, and asubstituted or unsubstituted heteroarylene of 2 to 20 carbon atoms; and

k is an integer of 1 to 3, wherein when k is 2 or greater, thecorresponding L₁₃'s are the same or different.

In this case, L₁₃ may be a single bond or a substituted or unsubstitutedarylene of 6 to 20 carbon atoms, and k may be 1 or 2, with the provisothat when k is 2, corresponding L₁₃'s may be the same or different.

For a more exemplary host, Ar₉ in Chemical Formula D may be asubstituent represented by the following Chemical Formula D-1:

wherein, R₂₁ to R₂₅, which may be the same or different, are as definedfor R₃ to R₅, above; and may each be linked to an adjacent one to form asaturated or unsaturated cyclic ring.

According to one embodiment, the anthracene derivative may be any oneselected from the compounds represented by the following <ChemicalFormula D1> to <Chemical Formula D48>:

In a particular embodiment thereof, the present invention provides anorganic light-emitting diode comprises: an anode as a first electrode; acathode as a second electrode facing the first electrode; and an organiclayer interposed between the anode and the cathode, wherein the organiclayer comprises at least one of the boron compounds represented byChemical Formulas A to C as a dopant and at least one of the compoundsrepresented by Chemical Formula D. Having such structuralcharacteristics, the organic light-emitting diode according to thepresent disclosure can be driven at a low voltage with high luminousefficiency.

The content of the dopant in the light-emitting layer may range fromabout 0.01 to 20 parts by weight, based on 100 parts by weight of thehost, but is not limited thereto.

In addition to the above-mentioned dopants and hosts, the light-emittinglayer may further include various hosts and dopant materials.

Below, the organic light-emitting diode of the present disclosure isexplained with reference to FIG. 1.

FIG. 1 is a schematic cross-sectional view of the structure of anorganic light-emitting diode according to an embodiment of the presentdisclosure.

As shown in FIG. 1, the organic light-emitting diode according to anembodiment of the present disclosure comprises an anode 20, a holetransport layer 40, an organic light-emitting layer 50 containing a hostand a dopant, an electron transport layer 60, and a cathode 80, whereinthe anode and the cathode serve as a first electrode and a secondelectrode, respectively, with the interposition of the two holetransport layer 40 between the anode and the light-emitting layer, andthe electron transport layer between the light-emitting layer and thecathode.

Furthermore, the organic light-emitting diode according to an embodimentof the present disclosure may comprise a hole injection layer 30 betweenthe anode 20 and the hole transport layer 40, and an electron injectionlayer 70 between the electron transport layer 60 and the cathode 80.

Reference is made to FIG. 1 with regard to the organic light emittingdiode of the present disclosure and the fabrication thereof.

First, a substrate 10 is coated with an anode electrode material to forman anode 20. So long as it is used in a typical organicelectroluminescence device, any substrate may be used as the substrate10. Preferable is an organic substrate or transparent plastic substratethat exhibits excellent transparency, surface smoothness, ease ofhandling, and waterproofness. As the anode electrode material, indiumtin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), or zincoxide (ZnO), which are transparent and superior in terms ofconductivity, may be used.

A hole injection layer material is applied on the anode 20 by thermaldeposition in a vacuum or by spin coating to form a hole injection layer30. Subsequently, thermal deposition in a vacuum or by spin coating mayalso be conducted to form a hole transport layer 40 with a holetransport layer material on the hole injection layer 30.

So long as it is typically used in the art, any material may be selectedfor the hole injection layer without particular limitations thereto.Examples include, but are not limited to, 2-TNATA[4,4′,4″-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD[N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine)], TPD[N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine], andDNTPD[N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine].

Any material that is typically used in the art may be selected for thehole transport layer without particular limitations thereto. Examplesinclude, but are not limited to,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD)and N,N′-di(naphthalen-1-yl)-N,N′-diphenylbenzidine (a-NPD).

In an embodiment of the present disclosure, an electron blocking layermay be additionally disposed on the hole transport layer. Functioning toprevent the electrons injected from the electron injection layer fromentering the hole transport layer from the light-emitting layer, theelectron blocking layer is adapted to increase the life span andluminous efficiency of the diode. The electron blocking layer may beformed of the compound represented by Chemical Formula E, the compoundrepresented by Chemical Formula F, a material known in the art, or acombination thereof at a suitable position between the light emittinglayer and the hole injection layer. Particularly, the electron blockinglayer may be formed between the light emitting layer and the holetransport layer.

Next, the light-emitting layer 50 may be deposited on the hole transportlayer 40 or the electron blocking layer by deposition in a vacuum or byspin coating.

Herein, the light-emitting layer may contain a host and a dopant and thematerials are as described above.

In some embodiments of the present disclosure, the light-emitting layerparticularly ranges in thickness from 50 to 2,000 Å.

Meanwhile, the electron transport layer 60 is applied on thelight-emitting layer by deposition in a vacuum and spin coating.

A material for use in the electron transport layer functions to stablycarry the electrons injected from the electron injection electrode(cathode), and may be an electron transport material known in the art.Examples of the electron transport material known in the art includequinoline derivatives, particularly, tris(8-quinolinolate)aluminum(Alq₃), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-olate) (Bebq₂),Compound 201, Compound 202, BCP, and oxadiazole derivatives such as PBD,BMD, and BND, but are not limited thereto:

In the organic light emitting diode of the present disclosure, anelectron injection layer (EIL) that functions to facilitate electroninjection from the cathode may be deposited on the electron transportlayer. The material for the EIL is not particularly limited.

Any material that is conventionally used in the art can be available forthe electron injection layer without particular limitations. Examplesinclude CsF, NaF, LiF, Li₂O, and BaO. Deposition conditions for theelectron injection layer may vary, depending on compounds used, but maybe generally selected from condition scopes that are almost the same asfor the formation of hole injection layers.

The electron injection layer may range in thickness from about 1 Å toabout 100 Å, and particularly from about 3 Å to about 90 Å. Given thethickness range for the electron injection layer, the diode can exhibitsatisfactory electron injection properties without actually elevating adriving voltage.

In order to facilitate electron injection, the cathode may be made of amaterial having a small work function, such as metal or metal alloy suchas lithium (Li), magnesium (Mg), calcium (Ca), an alloy aluminum (Al)thereof, aluminum-lithium (Al—Li), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag). Alternatively, ITO or

IZO may be employed to form a transparent cathode for an organiclight-emitting diode.

Moreover, the organic light-emitting diode of the present disclosure mayfurther comprise a light-emitting layer containing a blue, green, or redluminescent material that emits radiations in the wavelength range of380 nm to 800 nm. That is, the light-emitting layer in the presentdisclosure has a multi-layer structure wherein the blue, green, or redluminescent material may be a fluorescent material or a phosphorescentmaterial.

Furthermore, at least one selected from among the layers may bedeposited using a single-molecule deposition process or a solutionprocess.

Here, the deposition process is a process by which a material isvaporized in a vacuum or at a low pressure and deposited to form alayer, and the solution process is a method in which a material isdissolved in a solvent and applied for the formation of a thin film bymeans of inkjet printing, roll-to-roll coating, screen printing, spraycoating, dip coating, spin coating, etc.

Also, the organic light-emitting diode of the present disclosure may beapplied to a device selected from among flat display devices, flexibledisplay devices, monochrome or grayscale flat illumination devices, andmonochrome or grayscale flexible illumination devices.

A better understanding of the present disclosure may be obtained throughthe following examples which are set forth to illustrate, but are not tobe construed as limiting the present invention.

EXAMPLES Synthesis Example 1: Synthesis of Compound 1 Synthesis Example1-1: Synthesis of [Intermediate 1-a]

In a round-bottom flask, phenylhydrazine (100 g, 0.924 mol) and aceticacid (500 ml) were stirred and heated to 60° C. Slow addition of dropsof 2-methyl cyclohexanone (103.6 g, 0.924 mol) were followed by stirringunder reflux for 8 hours. After completion of the reaction, extractionwas made using water and ethyl acetate and the extract was concentratedand isolated by column chromatography to afford [Intermediate 1-a] (130g, yield 76%).

Synthesis Example 1-2: Synthesis of [Intermediate 1-b]

In a round-bottom flask, [Intermediate 1-a] (75 g, 405 mmol) was addedto toluene (750 ml) and chilled to −10° C., followed by slowly addingdrops of 1.6 M methyl lithium (380 ml, 608 mmol) and stirring at −10° C.for 3 hours. After completion of the reaction, extraction was made usingwater and ethyl acetate and the extract was concentrated and isolated bycolumn chromatography to afford [Intermediate 1-b] (50.5 g, yield 62%).

Synthesis Example 1-3. Synthesis of [Intermediate 1-c]

In a round-bottom flask, [Intermediate 1-b] (50 g, 251 mmol),1-bromo-2,3-dichlorobenzene (56.7 g, 251 mmol), trisdibenzylideneacetone dipalladium (4.5 g, 5 mmol), tri-tert-butyl phosphine (2 g, 10mmol), sodium tert-butoxide (35.8 g, 373 mmol), and toluene (500 ml)were fluxed for 24 hours under a nitrogen atmosphere. After completionof the reaction, the organic layer was concentrated and isolated bycolumn chromatography to afford [Intermediate 1-c]. (35.6 g, yield 41%)

Synthesis Example 1-4. Synthesis of [Intermediate 1-d]

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using diphenylamine and [Intermediate 1-c] instead of[Intermediate 1-b] and 1-bromo-2,3-dichlorobenzene, respectively, toafford [Intermediate 1-d]. (yield 73%)

Synthesis Example 1-5. Synthesis of [Compound 1]

In a round-bottom flask, tert-butyl benzene (200 ml) was added with[Intermediate 1-d] (20 g, 42 mmol) under a nitrogen atmosphere, andchilled to −30° C., followed by slow addition of drops of 1.7 Mtert-butyl lithium pentane solution (49.1 mml, 84 mmol). After thedropwise addition, the mixture was heated to 60° C., stirred for 3hours, and subjected to distillation to remove pentane. Drops of borontribromide (20.8 g, 84 mmol) were added at −50° C. and stirred for hourat room temperature. Addition of drops of N, N-diisopropylethylamine(10.7 g, 84 mmol) at 0° C. was followed by stirring for 2 hours at 120°C. After completion of the reaction, tert-butylbenzene was removed byvacuum distillation. Following extraction with ethyl acetate and water,the organic layer was concentrated and isolated by column chromatographyto afford [Compound 1]. (5.3 g, yield 28%)

MS (MALDI-TOF): m/z 452.24 [M⁺]

Synthesis Example 2: Synthesis of Compound 37 Synthesis Example 2-(1):Synthesis of [Intermediate 2-a]

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using 1-bromo-2-chloro-3-fluorobenzene instead of1-bromo-2,3-dichlorobenzene to afford [Intermediate 2-a]. (yield 58%)

Synthesis Example 2-(2): Synthesis of [Intermediate 2-b]

In a nitrogen atmosphere, phenol (39 g, 389 mmol), [Intermediate 2-a](129 g, 389 mmol), and potassium carbonate (80.7 g, 583 mmol) were addedto 1-methyl-2-pyrrolidinone (500 ml) and the mixture was stirred at 150°C. for 12 hours. After completion of the reaction, the organic layer wasconcentrated in a vacuum and isolated by column chromatography to afford[Intermediate 2-b]. (71.5 g, 65%)

Synthesis Example 2-(3): Synthesis of [Compound 37]

The same procedure as in Synthesis Example 1-5 was carried out, with theexception of using [Intermediate 2-b] instead of [Intermediate 1-d], tosynthesize [Compound 37]. (yield 71%)

MS (MALDI-TOF): m/z 377.20 [M⁺]

Synthesis Example 3: Synthesis of Compound 77 Synthesis Example 3-(1):Synthesis of [Intermediate 3-a]

The same procedure as in Synthesis Example 2-2 was carried out, with theexception of using 2-thiocresol instead of phenol, to afford[Intermediate 3-a]. (yield 63%)

Synthesis Example 3-(2): Synthesis of [Compound 77]

The same procedure as in Synthesis Example 1-5 was carried out, with theexception of using [Intermediate 3-a] instead of [Intermediate 1-d], toafford [Compound 77]. (yield 69%)

MS (MALDI-TOF): m/z 407.19 [M⁺]

Synthesis Example 4: Synthesis of Compound 33 Synthesis Example 4-(1):Synthesis of [Intermediate 4-a]

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using 2,3-dimethyl-2,3-dihydro-1H-indole instead of[Intermediate 1-b], to afford [Intermediate 4-a]. (yield 52%)

Synthesis Example 4-(2): Synthesis of [Intermediate 4-b]

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using N,N,N-triphenylbenzene-1,3,-diamine and [Intermediate4-a] instead of [Intermediate 1-b] and 1-bromo-2,3-dichlorobenzene,respectively, to afford [Intermediate 4-b]. (yield 55%)

Synthesis Example 4-(3): Synthesis of [Compound 33]

The same procedure as in Synthesis Example 1-5 was carried out, with theexception of using [Intermediate 4-b] instead of [Intermediate 1-d], toafford [Compound 33]. (yield 68%)

MS (MALDI-TOF): m/z 565.27 [M⁺]

Synthesis Example 5: Synthesis of Compound 13 Synthesis Example 5-(1):Synthesis of [Intermediate 5-a]

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using 1,2,3,4-tetrahydroisoquinoline instead W of[Intermediate 1-b], to afford [Intermediate 5-a]. (yield 63%)

Synthesis Example 5-(2): Synthesis of [Intermediate 5-b]

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using 4-aminobiphenyl and 1-bromodibenzofuran instead of[Intermediate 1-b] and 1-bromo-2,3-dichlorobenzene, respectively, toafford [Intermediate 5-b]. (yield 61%)

Synthesis Example 5-(3): Synthesis of [Intermediate 5-c]

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using [Intermediate 5-b] and [Intermediate 5-a] instead of[Intermediate 1-b] and 1-bromo-2,3-dichlorobenzene, respectively, toafford [Intermediate 5-c]. (yield 67%)

Synthesis Example 5-(4): Synthesis of [Compound 13]

The same procedure as in Synthesis Example 1-5 was carried out, with theexception of using [Intermediate 5-c] instead of [Intermediate 1-d], toafford [Compound 13]. (yield 66%)

MS (MALDI-TOF): m/z 550.22 [M⁺]

Synthesis Example 6: Synthesis of Compound 72 Synthesis Example 6-(1):Synthesis of [Intermediate 6-a]

The same procedure as in Synthesis Example 1-1,1-2 were carried out,with the exception of using 2-methylcycloheptanone instead of2-methylcyclohexanone, to afford [Intermediate 6-a]. (yield 72%)

Synthesis Example 6-(2): Synthesis of [Intermediate 6-b]

The same procedure as in Synthesis Example 2-1 was carried out, with theexception of using [Intermediate 6-a] instead of [Intermediate 1-b], toafford [Intermediate 6-b]. (yield 62%)

Synthesis Example 6-(3): Synthesis of [Intermediate 6-c]

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using diphenylamine and 7-chloronaphthalene-2-thiol insteadof [Intermediate 1-b] and 1-bromo-2,3-dichlorobenzene, respectively, toafford [Intermediate 6-c]. (yield 66%)

Synthesis Example 6-(4): Synthesis of [Intermediate 6-d]

The same procedure as in Synthesis Example 2-2 was carried out, with theexception of using [Intermediate 6-b] [Intermediate 6-c] W instead of[Intermediate 2-a] and phenol, respectively, to afford [Intermediate6-d]. (yield 69%)

Synthesis Example 6-(5): Synthesis of [Compound 72]

The same procedure as in Synthesis Example 1-5 was carried out, with theexception of using [Intermediate 6-d] instead of [Intermediate 1-d], toafford [Compound 72]. (yield 66%)

MS (MALDI-TOF): m/z 624.28 [M⁺]

Synthesis Example 7: Synthesis of Compound 91

The same procedures as in Synthesis Examples 1-1 to 1-5 were carriedout, with the exception of using 1-bromo-2,3-dichloro-5-methylbenzeneand bis(4-tert-butylphenyl)amine instead of 1-bromo-2,3-dichlorobenzeneof Synthesis Example 1-3 and diphenylamine of Synthesis Example 1-4,respectively, to afford [Compound 91]. (yield 15%)

MS(MALDI-TOF): m/z 578.38 [M⁺]

Synthesis Example 8: Synthesis of Compound 95

The same procedures as in Synthesis Example 1-1 to 1-5 was carried out,with the exception of using N1,N2,N3-triphenyl-1,3-benzenediamineinstead of diphenylamine of Synthesis Example 1-4, to afford [Compound95]. (yield 17%)

MS(MALDI-TOF): m/z 619.32 [M⁺]

Synthesis Example 9: Synthesis of Compound 96

The same procedures as in Synthesis Example 1-1 to 1-5 were carried out,with the exception of using [4-(1,1-dimethylethyl)phenyl]hydrazine andN1,N2,N3-triphenyl-1,3-benzene diamine instead of phenyl hydrazine ofSynthesis Example 1-1 and diphenylamine of Synthesis Example 1-4, toafford [Compound 96]. (yield 22%)

MS(MALDI-TOF): m/z 675.38 [M⁺]

Synthesis Example 10: Synthesis of Compound 100

The same procedure as in Synthesis Example 1-3 was carried out, with theexception of using 1-bromo-2,3-dichloro-5-tert-butyl benzene andN1,N2,N3-triphenyl-1,3-benzene diamine instead of1-bromo-2,3-dichlorobenzene of Synthesis Example 1-3 and diphenylamineof Synthesis Example 1-4, respectively, to afford [Compound 100]. (yield21%)

MS(MALDI-TOF): m/z 675.38 [M⁺]

Examples 1-12: Fabrication of Organic Light-Emitting Diodes

An ITO glass substrate was patterned to have a translucent area of 2mm×2 mm and cleansed. The ITO glass was mounted in a vacuum chamber thatwas then set to have a base pressure of 1×10⁻⁷ torr. On the ITO glasssubstrate, films were sequentially formed of DNTPD (700 Å) and [ChemicalFormula H] (300 Å). Subsequently, a light-emitting layer (250 Å) wasformed of a combination of [Chemical Formula BH1] and the boron compound(3 wt %) of the present disclosure. Then, [Chemical Formula E-1] and[Chemical Formula E-2] was deposited at a weight ratio of 1:1 to form anelectron transport layer (300 Å) on which an electron injection layer of[Chemical Formula E-1] (5 Å) was formed and then covered with an Allayer (1000 Å) to fabricate an organic light-emitting diode.

The organic light-emitting diodes thus obtained were measured at 0.4 mAfor luminescence properties:

Comparative Examples 1-3

Organic light emitting diodes were fabricated in the same manner as inthe Examples 1-12, with the exception of using [BD1] to [BD3] as dopantsinstead of the compounds according to the present disclosure. Theluminescence of the organic light-emitting diodes W thus obtained wasmeasured at 0.4 mA. Structures of compounds [BD1] to [BD3] are asfollows:

The organic light emitting diodes fabricated in Examples 1 to andComparative Examples 1 to 3 were measured for driving voltage, ExternalQuantum Efficiency and life span, and the results are summarized inTable 1, below.

TABLE 1 Current External Density Volt. Quantum T90 Example # Dopant(mA/cm²) (V) Efficiency (%) (hr) 1 Cpd. 1 10 3.99 8.7 162 2 Cpd. 3 104.03 8.6 159 3 Cpd. 13 10 4.07 8.3 176 4 Cpd. 18 10 4.01 8.9 181 5 Cpd.33 10 4.05 8.3 190 6 Cpd. 37 10 4.03 8.4 175 7 Cpd. 72 10 4.03 8.7 166 8Cpd. 77 10 3.98 8.1 192 9 Cpd. 91 10 4.01 8.7 192 10 Cpd. 95 10 4.03 8.9210 11 Cpd. 96 10 3.99 9.1 230 12 Cpd. 100 10 4.01 9.0 217 C. 1 BD1 104.17 7.5 142 C. 2 BD2 10 4.22 7.1 137 C. 3 BD3 10 4.15 5.8 88

As is understood from data of Table 1 for Examples 1 to 12, the boroncompounds according to the present disclosure allow low-voltage drivingand high quantum efficiency compared to Comparative Examples 1 to 3,thus finding high availability for organic light-emitting diodes.

1. A boron compound represented by any one of the following ChemicalFormulas A to C:

wherein, Q₁ to Q₃, which are same or different, are each independently asubstituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbonatoms, or a substituted or unsubstituted heteroaromatic ring of 2 to 50carbon atoms, Y is any one selected from N—R₃, CR₄R₅, O, S, and Se, X isany one selected from B, P and P═O and R₃ to R₅, which are same ordifferent, are each independently any one selected from a hydrogen atom,a deuterium, a substituted or unsubstituted alkyl of 1 to 30 carbonatoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, asubstituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, asubstituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, asubstituted or unsubstituted alkoxy of 1 to 30 carbon atoms, asubstituted or unsubstituted aryloxy of 6 to 30 carbon atoms, asubstituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, asubstituted or unsubstituted arylthioxy of 5 to 30 carbon atoms, asubstituted or unsubstituted alkylamine of 1 to 30 carbon atoms, asubstituted or unsubstituted arylamine of 5 to 30 carbon atoms, asubstituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, a nitro,a cyano, and a halogen, R₃ to R₅ are each connected to the Q₂ ringmoiety or Q₃ ring moiety to form an additional mono- or polycyclicaliphatic or aromatic ring and R₄ and R₅ are connected to each other toform an additional mono- or polycyclic aliphatic or aromatic ring, Cy1is a substituted or unsubstituted alkylene of 1 to 10 carbon atoms toform a ring with the nitrogen (N) atom, the aromatic carbon atom of Q₁to which the nitrogen (N) atom is connected, and the aromatic carbonatom of Q₁ to which Cy1 is to bond, Cy2 in Chemical formula B is asubstituted or unsubstituted alkylene of 1 to 10 carbon atoms to form asaturated hydrocarbon ring added to Cy1, together with the carbon atomsof Cy1, and Cy3 in Chemical Formula C is a substituted or unsubstitutedalkylene of 1 to 10 carbon atoms to form a ring with the aromatic carbonatom of Q₃ to which Cy3 is to bond, the aromatic carbon atom of Q₃ towhich the nitrogen (N) atom is connected, the nitrogen (N) atom, and thecarbon atom of Cy1 to which the nitrogen (N) atom is connected, wherein,the term ‘substituted’ in the expression “substituted or unsubstituted”used for compounds of Chemical Formulas A to C means having at least onesubstituent selected from the group consisting of a deuterium atom, acyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 24 carbon atoms,a halogenated alkyl of 1 to 24 carbon atoms, an alkenyl of 2 to 24carbon atoms, an alkynyl of 2 to 24 carbon atoms, a heteroalkyl of 1 to24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2to 50 carbon atoms, a heteroarylalkyl of 2 to 24 carbon atoms, an alkoxyof 1 to 24 carbon atoms, an alkylamino of 1 to 24 carbon atoms, anarylamino of 6 to 24 carbon atoms, a heteroarylamino of 1 to 24 carbonatoms, an alkylsilyl of 1 to 24 carbon atoms, an arylsilyl of 6 to 24carbon atoms, and an aryloxy of 6 to 24 carbon atoms.
 2. The boroncompound of claim 1, wherein Yin Chemical Formulas A to C is N—R₃wherein R₃ is as defined in claim
 1. 3. The boron compound of claim 2,wherein R₃ is a substituted or unsubstituted aryl of 6 to 50 carbonatoms or a substituted or unsubstituted heteroaryl of 2 to 50 carbonatoms.
 4. The boron compound of claim 1, wherein Y in Chemical FormulasA to C is a linker represented by the following Structural Formula A:

wherein “—*” denotes a bonding site at which the linker Y bonds to anaromatic carbon atom within the Q₂ and Q₃ ring moieties, R₄₁ to R₄₅,which are same or different, are each independently any one selectedfrom a hydrogen atom, a deuterium atom, a substituted or unsubstitutedalkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbonatoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, asubstituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, asubstituted or unsubstituted arylthioxy of 5 to 30 carbon atoms, asubstituted or unsubstituted alkylamine of 1 to 30 carbon atoms, asubstituted or unsubstituted arylamine of 5 to 30 carbon atoms, asubstituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, a nitro,a cyano, and a halogen.
 5. The boron compound of claim 1, wherein YinChemical Formulas A to C is an oxygen (O) atom.
 6. The boron compound ofclaim 1, wherein X in Chemical Formulas A to C is a boron (B) atom. 7.The boron compound of claim 1, wherein the Q₁ to Q₃ ring moieties, whichare same or different, are each independently a substituted orunsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms.
 8. Theboron compound of claim 7, wherein the aromatic hydrocarbon ring moietyQ₂ in Chemical Formulas A to C is any one selected from compoundsrepresented by the following Structural Formulas 10 to 21:

wherein, “—*” denotes a bonding site at which a carbon atom in thearomatic ring of Q₂ bonds to X and the linker Y, R's, which are same ordifferent, are each independently a hydrogen, a deuterium, a substitutedor unsubstituted alkyl of 1 to 30 carbon atoms, a substituted orunsubstituted aryl of 6 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted arylamine of 5 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted orunsubstituted arylsilyl of 5 to 30 carbon atoms, a cyano, and a halogen,and m is an integer of 1 to 8, wherein when m is two or more or two ormore R's are present, the corresponding R's are same or different. 9.The boron compound of claim 7, wherein the aromatic hydrocarbon rings ofQ₁ and Q₃ in Chemical Formulas A and B are same or different and areeach independently a ring represented by the following StructuralFormula B, and the aromatic hydrocarbon ring of Q₁ in Chemical Formula Cis a ring represented by the following Structural Formula B:

wherein “—*” denotes bonding sites at which the corresponding carbons inthe aromatic ring of Q₁ bond to X, the nitrogen (N) atom, and Cy1,respectively or at which the corresponding carbons in the aromatic ringin Q₃ bond to X, the linker Y, and the nitrogen (N) atom, respectively,and R₅₅ to R₅₇, which are same or different, are each independently anyone selected from a hydrogen, a deuterium, a substituted orunsubstituted alkyl of 1 to 30 carbon atoms, a substituted orunsubstituted aryl of 6 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted arylamine of 5 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted orunsubstituted arylsilyl of 5 to 30 carbon atoms, a cyano, and a halogen,and any adjacent two of R₅₅ to R₅₇ may be linked to each to each otherto form an additional mono- or polycyclic aliphatic or aromatic ring.10. The boron compound of claim 7, wherein the aromatic hydrocarbon ringof Q₃ in Chemical Formula C is represented by the following StructuralFormula C:

wherein, “—*” denotes bonding sites at which the corresponding carbonsin the aromatic ring of Q₃ bond to the linker Y, X, the nitrogen (N)atom, and Cy3, respectively, and R₅₈ and R₅₉, which are same ordifferent, are each independently any one selected from a hydrogen atom,a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbonatoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, asubstituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, asubstituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, asubstituted or unsubstituted alkoxy of 1 to 30 carbon atoms, asubstituted or unsubstituted aryoxy of 6 to 30 carbon atoms, asubstituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, asubstituted or unsubstituted arylthioxy of 5 to 30 carbon atoms, asubstituted or unsubstituted alkylamine of 1 to 30 carbon atoms, asubstituted or unsubstituted arylamine of 5 to 30 carbon atoms, asubstituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, a cyano,and a halogen, and R₅₈ and R₅₉ can be linked to each other to form anadditional mono- or polycyclic aliphatic or aromatic ring.
 11. The boroncompound of claim 1, wherein Cy1, which forms a ring with the nitrogen(N) atom and a carbon atom of the aromatic ring of Q1 in ChemicalFormulas A to C, is a linker represented by Structural Formula D:

wherein “—*” denotes a bonding site to a carbon within the aromatic ringof Q₁ or to the nitrogen atom, B is a single bond or —C(R₆₅)(R₆₆)— or—C(R₆₅)(R₆₆)—C(R₆₇)(R₆₈)—, and substituents R₆₁ to R₆₈, which may be thesame or different, are each independently selected from a hydrogen atom,a deuterium atom, a halogen, a substituted or unsubstituted alkyl of 1to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 20carbon atoms, a substituted or unsubstituted aryl of 6 to 20 carbonatoms, a substituted or unsubstituted heteroaryl of 2 to 20 carbonatoms, a substituted or unsubstituted alkylsilyl of 1 to 20 carbonatoms, a substituted or unsubstituted arylsilyl of 6 to 320 carbonatoms, wherein the term ‘substituted in the expression “substituted orunsubstituted” used is as defined in claim
 1. 12. The boron compound ofclaim 1, wherein the ring formed by Cy1, Cy2, the nitrogen atom, and Q1in Chemical Formula B is a ring represented by the following StructuralFormula E:

wherein, “—*” denotes a bonding site to a carbon atom within thearomatic ring of Q₃, B is a single bond or —C(R₆₅)(R₆₆)— or—C(R₆₅)(R₆₆)—C(R₆₇)(R₆₈)—, Substituents R₆₃ to R₆₈, which may be thesame or different, are each independently selected from a hydrogen atom,a deuterium atom, a halogen, a substituted or unsubstituted alkyl of 1to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 20carbon atoms, a substituted or unsubstituted aryl of 6 to 20 carbonatoms, a substituted or unsubstituted heteroaryl of 2 to 20 carbonatoms, a substituted or unsubstituted alkylsilyl of 1 to 20 carbonatoms, a substituted or unsubstituted arylsilyl of 6 to 320 carbonatoms, and Cy₄ is a substituted or unsubstituted alkylene of 2 to 5carbon atoms, with a methylene (—CH₂—) given for each end, wherein theterm ‘substituted’ in the expression “substituted or unsubstituted” usedis as defined in claim
 1. 13. The boron compound of claim 1, wherein atleast one of Q1 to Q3 in Chemical Formulas A to C is an aromatichydrocarbon ring of 6 to 50 carbon atoms or an aromatic heteroring of 2to 50 carbon atoms, each having an arylamino represented the followingStructural Formula F bonded thereto:

wherein, “—*” denotes a bonding site to at least one of Q₁ to Q₃, andAr₁₁ and Ar₁₂, which are same or different, are each independently asubstituted or unsubstituted aryl of 6 to 12 carbon atoms.
 14. The boroncompound of claim 1, wherein the boron compound is any one selected fromthe following <Compound 1> to <Compound 132>:


15. An organic light-emitting diode, comprising: a first electrode; asecond electrode facing the second electrode; and an organic layerinterposed between the first electrode and the second electrode, whereinthe organic layer includes a boron compound of claim
 1. 16. The organiclight-emitting diode of claim 15, wherein the organic layer comprises atleast one of a hole injection layer, a hole transport layer, afunctional layer capable of both hole injection and hole transport, anelectron blocking layer, a light-emitting layer, an electron transportlayer, an electron injection layer, and a capping layer.
 17. The organiclight-emitting diode of claim 15, wherein the organic layer disposedbetween the first electrode and the second electrode includes alight-emitting layer composed of a host and a dopant, the boron compoundrepresented by any one of Chemical Formulas A to C servings as thedopant.
 18. The organic light-emitting diode of claim 15, wherein thelight-emitting layer uses an anthracene derivative represented by thefollowing Chemical Formula D as the host:

wherein, R₁₁ to R₁₈, which are same or different, are each as definedfor R₃ to R₅ in claim 1; Ar₉ and Ar₁₀, which are same or different, areeach independently any one selected from a hydrogen atom, a deuteriumatom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, asubstituted or unsubstituted aryl of 6 to 50 carbon atoms, a substitutedor unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted orunsubstituted alkynyl 2 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted orunsubstituted cycloalkenyl 5 to 30 carbon atoms, a substituted orunsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted orunsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted orunsubstituted alkoxy of 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted orunsubstituted arylthioxy of 6 to 30 carbon atoms, a substituted orunsubstituted alkylamine of 1 to 30 carbon atoms, a substituted orunsubstituted aryamine of 6 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl of 1 to 30 carbon atoms, and a substituted orunsubstituted arylsilyl of 6 to 30 carbon atoms; L₁₃, which functions asa linker, is a single bond or is selected from a substituted orunsubstituted arylene of 6 to 20 carbon atoms, and a substituted orunsubstituted heteroarylene of 2 to 20 carbon atoms; and k is an integerof 1 to 3, wherein when k is 2 or greater, the corresponding L₁₃'s aresame or different.
 19. The organic light-emitting diode of claim 18,wherein Arg in Chemical Formula D is a substituent represented by thefollowing Chemical Formula D-1:

wherein, R₂₁ to R₂₅, which are same or different, are as defined for R₃to R₅ in claim 1; and can each be linked to an adjacent one to form asaturated or unsaturated cyclic ring.
 20. The organic light-emittingdiode of claim 18, wherein Lia is a single bond or a substituted orunsubstituted arylene of 6 to 20 carbon atoms, and k is 1 or 2, with theproviso that when k is 2, corresponding L₁₃'s are same or different. 21.The organic light-emitting diode of claim 15, wherein the anthracenederivative is any one selected from the compounds represented by thefollowing [Chemical Formula D1] to [Chemical Formula D48]:


22. The organic light-emitting diode of claim 16, wherein at least oneselected from among the layers is deposited using a single-moleculedeposition process or a solution process.
 23. The organic light-emittingdiode of claim 15, wherein the organic light-emitting diode is used fora device selected from among a flat display device; a flexible displaydevice; a monochrome or grayscale flat illumination; and a monochrome orgrayscale flexible illumination device.